‘Send Mail As’ with Gmail – Fixing the Authentication Failed Error

Below you’ll learn how to fix the Gmail Server error which appears when adding a Google Apps account inside of a personal Gmail account. Full tutorial is below along with a step by step video at the end of the post.

If you’re using Google Apps, and have tried to set up your Google Apps email account inside of a second personal Gmail account, you may have run into an error similar to this one:

Step 2.

Once you’re in. Click ‘Security’. If you can’t see it, type Security into the search field at the top of the Admin Console.

Click Security from the admin panel or Search using the box at the top

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Step 3.

Step 4.

Click the “Go to settings for less secure apps ››” link next to Less Secure Apps‘

Click the Less Secure Apps Link

Step 5.

If it’s not set already. change the setting on this page to “Allow users to manage their access to less secure apps“. If this is already set, don’t worry, there’s another change we need to make before everything will start to work :-). Once you’re done. Press ‘SAVE‘ in the bottom right.

Ensure ‘Allow users to manage their access to less secure apps’ is set

Step 6.

Next we need to access the ‘My Account’ page for the Google Apps user you’re trying to add to your personal gmail account. So if you’re trying to add ‘ben@mydomain.com’ to ben@gmail.com, you need to be signed into ben@mydomain.com. This may well be your Google Apps Administrator account too, In which case, you’re already signed in.

If it is the same account, and you’re already signed in, you can access the my account page by clicking the icon in the top right hand corner of the screen you’re on, then clicking the blue ‘My Account’ button. If it’s a different account, you simply need to sign in via https://myaccount.google.com/.

Access My Account from the top right, or sign in via https://myaccount.google.com/

Step 7.

Step 8.

From the left hand menu on the Sign In and Security Page, click ‘Connected Apps & Sites’

Click ‘Connected Apps & Sites’

Step 9.

Scroll down on the Connected Apps and Sites section and in the last box you’ll see the title ‘Allow less secure apps: on/off’ – press the switch to the right to make it go blue. So the title Reads ‘Allow Less Secure Apps: ON’

Check Allow Less Secure Apps to ON

Step 10.

Log out of your Google Apps user account and visit www.gmail.com. Enter your personal gmail username and password to login. Once you’re in, press the cog in the top right hand corner. Then click on the ‘Accounts and Import’ tab. Inside the ‘Send Mail As’ section click on ‘Add another email address that you own’.

Gmail – Add another address that you own

Step 11.

In the pop up window that appears, enter your name and the email address, then click on ‘Next Step’.

Add another email address that you own

Step 12.

In the next window, enter ‘smtp.gmail.com’ as the SMTP server. Then enter the email address and password of the google apps user account you’re trying to add. Then press ‘Add Account’.

Enter your google apps user account info

Step 13.

On the next screen, if the account has been successfully added you’ll be asked to enter a verification code. This code will have been emailed to the Google Apps user email account you’ve just added. Log in to that account and grab the code, then enter it in the box. Or alternatively, click the link included in the email to verify your account. And that’s it. Job done 🙂 Make yourself a brew.

Gmail – Confirm verification and email address.

Step by step video tutorial.

Below you’ll find a full video which takes you through the entire process of adding a Google Apps email address to a personal Gmail account.

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Hey Evie, no you need to leave less secure apps set to on. If you turn that off it’ll stop working again. Goodness knows why google considers Gmail to be a ‘less secure app’!

emailevie September 17, 2016 at 8:20 pm

Hi Ben, thanks for your reply, in the admin console I set it back to ‘Disable access to less secure apps for all users’ and now there is no option in MY Account to turn OFF ‘Allow less secure apps’. This should be ok anyway?

That’s an interesting point, the first setting is you as an admin preventing users under your domain from accessing the setting which allows them to enable less secure apps to their accounts. It’s a security feature offered to admins to help protect their users.

Logic would suggest that if you as the admin user turn it off, that not only will it remove the setting from your user’s accounts tabs, but it would also turn off the setting, effectively breaking any apps accounts set up in Gmail accounts.

That being said i’ve not tested that exact scenario, so I’d be keen to know what happened when you tested it. But I’d put my money on it breaking things.

I’m attempting to do the reverse of this, have Google Apps send from a Gmail address.

While Less Secure Apps are enabled on the gmail account, sending emails bounces back with the following details:

Google tried to deliver your message, but it was rejected by the relay smtp.gmail.com [IP]

From what I can tell, looking into the Gmail Accounts security settings, SMTP.Gmail.com is blocking the IP address of the server that the Google Apps account is attempting to send from. As there are “Suspicious access blocked” logs occurring, coinciding with attempts to send emails.

Any ideas on how to resolve this?

Jason Draut October 29, 2016 at 6:17 am

It took me over an hour of fighting and looking google support before I found this page, then it took me 3 minutes to get it to work properly. Thanks!

@Enric, Thanks for taking the time to comment! Glad you got it sorted 🙂

estulin February 9, 2017 at 8:12 pm

Works great but now I can’t use 2-step verification I get the following message.

Message not delivered
You’re sending this from a different address or alias using the ‘Send mail as’ feature. The settings for your ‘Send mail as’ account are misconfigured or out of date. Check those settings and try resending.

Is there a workaround?

Pizza March 29, 2017 at 5:30 am

But why… gmail is saying gmail is less secure??

Orion April 20, 2017 at 2:35 am

Thank you very much!

Dave May 11, 2017 at 4:13 pm

Ben, thank you VERY much!

You’re a life saver. What was interesting for me, is that it worked initially without your steps – but then it stopped after one day and the only way to get things straight again was following your instructions.

The one area that I ran into was in Step 9 the key that needed to be selected to change it to blue was not there. I thought it might have something to do with I had two-factor generation turned on. I generated a two-factor password and used that in Step 13 and now everything is fine.

It is unclear to me why two-factor might have that 3rd box on screen 9 so it does not show up, but I did not want to go back and turn off two-factor at this now that it is working (again).

Hi Pearls, You don’t need to repeat step 6 for every account, as that’s at the google apps admin overview level – but you will need to repeat steps 7 onwards for each gsuite account you wish to access via gmail SMTP.

Rajesh Prajapati September 19, 2017 at 5:13 pm

I Use my office mail (which is not google app) send as through gmail free version. What is the work around for that?

You, Sir, are a genius! After about an hour on phone with google rep and ticket escalations (to no avail), I am so lucky to have found your instructions. Mind if I share this with Google along with my case id? 😉

Of course, right after leaving this comment, I think I figured it out. The account I was setting up had two-factor authentication turned on. Turning it off made the missing section show up. It appears that turning two-factor off, then setting up the ability to send emails from my gmail account, and then re-enabling two-factor got me back to the place I wanted to be. In the future, if I hit problems, I’ll try generating a password for the gmail account to use to login.